NPASS Compound

Natural Product: NPC208217

Natural Product ID	NPC208217
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KHIZMXXBPIYCQP-CLBBDDOLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11607358
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 116123 0 0 0 0 0 0 0 0999 V2000 10.6252 -0.2395 -1.8542 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5141 -0.3439 -0.8342 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8217 -1.2841 0.2967 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6253 -1.9686 0.8622 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3035 -1.4341 0.4978 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5959 -0.6815 1.6484 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2648 0.6412 1.9355 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2646 -0.5215 1.0263 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2263 -1.7519 0.0928 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9055 -2.4627 0.4524 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1386 -1.2750 0.8139 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7736 -1.3269 1.3470 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9013 -2.3974 0.8155 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5483 -2.1125 1.2068 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8652 -0.7938 0.6170 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3112 -0.4057 0.5103 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3773 0.5382 -0.6640 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1957 1.5166 -0.5960 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5929 1.6166 0.7686 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1522 0.3238 1.3856 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4855 0.3391 2.8409 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2859 0.0936 1.1101 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2230 1.0833 1.7310 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4144 0.5358 2.4103 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0644 -0.6684 1.8845 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3244 -1.6626 2.9890 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2333 1.2308 -1.5800 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4872 1.2466 -0.8661 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1632 1.1330 -2.0375 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6033 0.7002 -1.9400 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0357 0.2213 -3.3021 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6837 1.2315 -4.3559 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3361 1.8276 -4.1420 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0172 2.8972 -5.1273 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6678 3.2538 -4.9144 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1615 2.2862 -2.8218 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6803 2.1881 -4.4923 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3739 -0.1381 -3.3763 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8085 -0.3092 -1.0201 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6677 0.0451 0.0031 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8607 -0.8412 0.1806 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4211 -0.7402 1.5885 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0436 0.6231 2.1234 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5346 0.6636 2.2229 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1077 2.1039 2.1002 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9309 -0.0401 1.1935 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5711 0.8348 3.3975 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8043 -0.9038 1.5222 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8676 -0.3677 -0.6717 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3427 -2.4807 0.3724 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2181 -0.6077 -0.5847 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2140 -0.6970 -1.5200 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6145 -0.1213 -1.3383 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6199 -1.1060 -2.5204 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4679 0.7260 -2.4140 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3920 0.6967 -0.4224 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5112 -2.0561 -0.1110 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4284 -0.7523 1.0841 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6304 -3.0644 0.5732 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7234 -1.9486 1.9824 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6929 -1.3205 2.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1418 0.8246 3.0338 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3331 0.6683 1.7273 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6858 1.4663 1.4378 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2483 0.4197 0.4402 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2068 -1.4415 -0.9617 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5100 -2.8789 -0.5093 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0350 -3.2550 1.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2389 -0.5574 -0.0576 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7335 -1.4360 2.4757 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9497 -2.5297 -0.2806 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1635 -3.3448 1.3340 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2302 -2.8671 0.7215 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6914 -2.2062 2.2786 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3703 -0.7862 -0.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5922 0.0787 1.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8752 -1.3515 0.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1790 -0.0933 -1.5749 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5396 2.5623 -0.8520 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2279 2.3316 0.7197 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3763 2.0934 1.4297 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5848 1.4073 3.1984 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4084 -0.1610 3.1265 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3214 -0.0907 3.4784 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3989 0.2218 -0.0116 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6275 1.6784 2.4588 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5728 1.8542 0.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1320 0.3625 3.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1884 1.3561 2.4732 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7044 -1.0701 3.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0339 -2.4532 2.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4118 -2.1694 3.3639 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5284 1.5240 -2.4740 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6236 0.3736 -2.6444 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1866 1.6172 -1.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3834 -0.6785 -3.5171 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6161 0.6540 -5.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5854 0.9867 -4.2256 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6506 3.7884 -5.0251 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0527 2.4965 -6.1545 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1742 2.3746 -4.9307 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9223 2.2896 -5.4471 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4234 -0.7739 -4.1611 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0296 1.0733 -0.0866 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6750 -1.8886 -0.1381 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9958 -1.4939 2.2787 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3896 1.3747 1.3993 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2089 0.2914 3.2140 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0263 2.2445 2.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3989 2.5453 1.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6780 2.6776 2.8773 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4432 0.3698 3.4624 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0244 -1.3501 0.6669 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8410 0.6044 -0.7982 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2860 -1.6493 -2.0556 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0149 0.1422 -2.2543 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 18 27 1 0 17 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 31 38 1 0 30 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 44 46 1 0 43 47 1 0 42 48 1 0 41 49 1 0 9 50 1 0 5 51 1 6 51 52 1 0 52 2 1 0 50 5 1 0 25 8 1 0 36 29 1 0 46 40 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 1 3 57 1 0 3 58 1 0 4 59 1 0 4 60 1 0 6 61 1 1 7 62 1 0 7 63 1 0 7 64 1 0 8 65 1 6 9 66 1 6 10 67 1 0 10 68 1 0 11 69 1 6 12 70 1 1 13 71 1 0 13 72 1 0 14 73 1 0 14 74 1 0 15 75 1 6 16 76 1 0 16 77 1 0 17 78 1 6 18 79 1 6 19 80 1 0 19 81 1 0 21 82 1 0 21 83 1 0 21 84 1 0 22 85 1 6 23 86 1 0 23 87 1 0 24 88 1 0 24 89 1 0 26 90 1 0 26 91 1 0 26 92 1 0 27 93 1 0 29 94 1 6 30 95 1 1 31 96 1 6 32 97 1 6 33 98 1 6 34 99 1 0 34100 1 0 35101 1 0 37102 1 0 38103 1 0 40104 1 6 41105 1 6 42106 1 1 43107 1 6 44108 1 1 45109 1 0 45110 1 0 45111 1 0 47112 1 0 48113 1 0 49114 1 0 52115 1 0 52116 1 0 M END

Standard InCHIKey	KHIZMXXBPIYCQP-CLBBDDOLSA-N
Standard InCHI	InChI=1S/C39H64O13/c1-17-8-11-39(47-16-17)18(2)28-26(52-39)13-23-21-7-6-20-12-25(24(41)14-38(20,5)22(21)9-10-37(23,28)4)49-36-34(32(45)30(43)27(15-40)50-36)51-35-33(46)31(44)29(42)19(3)48-35/h17-36,40-46H,6-16H2,1-5H3/t17-,18+,19+,20+,21-,22+,23+,24-,25-,26+,27-,28+,29+,30+,31-,32+,33-,34-,35+,36-,37+,38+,39-/m1/s1
SMILES	C[C@@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC[C@H]6C[C@H]([C@@H](C[C@]6(C)[C@H]5CC[C@]34C)O)O[C@H]3[C@@H]([C@H]([C@H]([C@@H](CO)O3)O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	740.43	Volume:	728.921 ? Van der Waals volume.
Dense:	1.016	LogP:	2.918 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.419 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.088 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	42.0
TPSA:	196.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	8.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.2	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.323	Fsp³:	1.0
MCE-18:	203.846 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.709	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.03 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.256	Promiscuous compounds:	0.031

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.933	MDCK Permeability:	-5.12
Pgp-inhibitor:	0.0	Pgp-substrate:	0.617
PAMPA:	0.999 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.223
20% Bioavailability (F20%):	0.876	30% Bioavailability (F30%):	0.967
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015	MRP1:	0.113
Plasma Protein Binding (PPB):	63.333%	Volume Distribution (VD):	-0.413
Fu:	29.548% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.292
BSEP inhibitor:	0.038

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.989
HLM stability:	0.375 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.838

Half-life (T1/2):

2.468

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.215
Human Hepatotoxicity (H-HT):	0.609	Drug-induced Liver Injury (DILI):	0.963
AMES Toxicity:	0.849	Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.089	Skin Sensitization:	1.0
Carcinogencity:	0.188	Eye Corrosion:	0.0
Eye Irritation:	0.011	Respiratory Toxicity:	0.022
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.987
Hematotoxicity:	0.241	Drug-induced Nephrotoxicity:	0.758
Genotoxicity:	0.005	RPMI-8226 Immunitoxicity:	0.272
A549 Cytotoxicity:	0.937	Hek293 Cytotoxicity:	0.91
BCF:	2.001 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.589 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.717 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.196 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662101]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15013012]
NPO22926	Centaurea moschata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20423	Euryops imbricatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19644	Dalea scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20836	Gentiana manshurica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10886	Spiranthera odoratissima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22926	Centaurea moschata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21760	Bungarus multicinctus	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19090	Polygonatum officinale	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21093	Sinularia gonatodes	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20423	Euryops imbricatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22474	Gnaphalium declinatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC208217 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	27173
0.1-0.2	19428
0.2-0.3	2628
0.3-0.4	424
0.4-0.5	93
0.5-0.6	70
0.6-0.7	26
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC222731
0.9487	High Similarity	NPC294686
0.8391	Intermediate Similarity	NPC195297
0.8214	Intermediate Similarity	NPC477451
0.814	Intermediate Similarity	NPC54619
0.7765	Intermediate Similarity	NPC297348
0.7765	Intermediate Similarity	NPC249204
0.7765	Intermediate Similarity	NPC48339
0.7765	Intermediate Similarity	NPC141769
0.7765	Intermediate Similarity	NPC477547
0.7174	Intermediate Similarity	NPC107962
0.7158	Intermediate Similarity	NPC473601
0.6957	Remote Similarity	NPC211354
0.6947	Remote Similarity	NPC113044
0.6947	Remote Similarity	NPC283829
0.6947	Remote Similarity	NPC161676
0.6915	Remote Similarity	NPC6295
0.6893	Remote Similarity	NPC83137
0.6774	Remote Similarity	NPC19400
0.6667	Remote Similarity	NPC141433
0.6569	Remote Similarity	NPC115165
0.6374	Remote Similarity	NPC485594
0.6344	Remote Similarity	NPC234352
0.6316	Remote Similarity	NPC206003
0.6316	Remote Similarity	NPC473610
0.6263	Remote Similarity	NPC160426
0.625	Remote Similarity	NPC306131
0.625	Remote Similarity	NPC200802
0.6237	Remote Similarity	NPC325828
0.6224	Remote Similarity	NPC485595
0.6222	Remote Similarity	NPC473774
0.6222	Remote Similarity	NPC481419
0.6222	Remote Similarity	NPC481417
0.6214	Remote Similarity	NPC151134
0.6154	Remote Similarity	NPC24960
0.6132	Remote Similarity	NPC475625
0.6019	Remote Similarity	NPC92890
0.6019	Remote Similarity	NPC477809
0.5981	Remote Similarity	NPC32361
0.5963	Remote Similarity	NPC470862
0.5926	Remote Similarity	NPC232611
0.5918	Remote Similarity	NPC107188
0.5905	Remote Similarity	NPC480555
0.5905	Remote Similarity	NPC128572
0.5905	Remote Similarity	NPC150372
0.5889	Remote Similarity	NPC144790
0.5889	Remote Similarity	NPC149400
0.5882	Remote Similarity	NPC475351
0.587	Remote Similarity	NPC481420
0.587	Remote Similarity	NPC481421
0.5824	Remote Similarity	NPC277715
0.5816	Remote Similarity	NPC121453
0.581	Remote Similarity	NPC471464
0.5769	Remote Similarity	NPC470433
0.5769	Remote Similarity	NPC46190
0.5769	Remote Similarity	NPC171073
0.5729	Remote Similarity	NPC177834
0.5701	Remote Similarity	NPC184617
0.5688	Remote Similarity	NPC473518
0.5686	Remote Similarity	NPC70204
0.566	Remote Similarity	NPC300557
0.5631	Remote Similarity	NPC14704
0.5625	Remote Similarity	NPC181845
0.5625	Remote Similarity	NPC480553
0.5619	Remote Similarity	NPC475643
0.5619	Remote Similarity	NPC602423
0.5586	Remote Similarity	NPC480554
0.5556	Remote Similarity	NPC97700
0.5556	Remote Similarity	NPC250393
0.5556	Remote Similarity	NPC30856
0.5556	Remote Similarity	NPC474399
0.551	Remote Similarity	NPC131693
0.551	Remote Similarity	NPC475436
0.5481	Remote Similarity	NPC305423
0.5455	Remote Similarity	NPC269297
0.5455	Remote Similarity	NPC222202
0.5447	Remote Similarity	NPC481190
0.5437	Remote Similarity	NPC125324
0.5437	Remote Similarity	NPC470432
0.5437	Remote Similarity	NPC230507
0.5433	Remote Similarity	NPC329820
0.5405	Remote Similarity	NPC475333
0.5405	Remote Similarity	NPC224098
0.5405	Remote Similarity	NPC208383
0.5403	Remote Similarity	NPC330026
0.5357	Remote Similarity	NPC227260
0.5354	Remote Similarity	NPC291203
0.5354	Remote Similarity	NPC217205
0.5351	Remote Similarity	NPC132080
0.5345	Remote Similarity	NPC470867
0.5306	Remote Similarity	NPC481424
0.5306	Remote Similarity	NPC481422
0.5278	Remote Similarity	NPC248746
0.5268	Remote Similarity	NPC13193
0.5254	Remote Similarity	NPC480556
0.5221	Remote Similarity	NPC194207
0.5221	Remote Similarity	NPC232037
0.5221	Remote Similarity	NPC22779
0.5192	Remote Similarity	NPC485601
0.5176	Remote Similarity	NPC248944
0.5176	Remote Similarity	NPC7479
0.5176	Remote Similarity	NPC257296
0.5091	Remote Similarity	NPC51172
0.5091	Remote Similarity	NPC49032
0.5052	Remote Similarity	NPC481418
0.5049	Remote Similarity	NPC128123
0.5043	Remote Similarity	NPC470864
0.5043	Remote Similarity	NPC31896

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC208217 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7660
0.1-0.2	1411
0.2-0.3	70
0.3-0.4	5
0.4-0.5	1
0.5-0.6	2
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6237	Remote Similarity	NPD8171	Phase 2
0.5437	Remote Similarity	NPD8170	Phase 2
0.5176	Remote Similarity	NPD6928	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data